Dibromomethane → 2-(1,3-Dithietan-2-ylidene)-2-phenyl-1-p-tolylethanone

HRID 1471901Notes

Reaction equation

HRID 1471901 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])(C)C.[K+].[C:23](=[S:25])=[S:24].Br[CH2:27]Br>C1COCC1>[S:24]1[CH2:27][S:25][C:23]1=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[O:9]

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 6348Carbon DisulfideHCID 2280161-(4-Methylphenyl)-2-phenylethan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 866575802-(1,3-Dithietan-2-ylidene)-2-phenyl-1-p-tolylethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-phenyl-1-p-tolylethanone (3.00 g, 14.27 mmol) in THF (50.0 mL) was added KOtBu (30.0 mL, 30.0 mmol), CS2 (0.862 mL, 14.27 mmol) and dibromomethane (0.994 mL, 14.27 mmol). The reaction was stirred at 25° C. for 12 h, quenched with water (40.0 mL) and extracted with EtOAc (3×50.0 mL). The combined organics were dried over MgSO4, filtered, and concentrated to give the title compound as a brown oil without further purification. LCMS m/z=299.2 [M+H]+.

Workup

  1. customquenched with water (40.0 mL)
  2. extractionextracted with EtOAc (3×50.0 mL)
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-14fb23a9150b4be7acbf6fba4caa287d
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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